EP0208403A1 - Water-dilutable disinfectant composition - Google Patents

Water-dilutable disinfectant composition Download PDF

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Publication number
EP0208403A1
EP0208403A1 EP86303884A EP86303884A EP0208403A1 EP 0208403 A1 EP0208403 A1 EP 0208403A1 EP 86303884 A EP86303884 A EP 86303884A EP 86303884 A EP86303884 A EP 86303884A EP 0208403 A1 EP0208403 A1 EP 0208403A1
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EP
European Patent Office
Prior art keywords
composition
acid
alcohol
carbon atoms
water
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP86303884A
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German (de)
French (fr)
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EP0208403B1 (en
Inventor
Thomas Rysiok
Florian Lichtenberg
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Diversey GmbH
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Diversey Corp Canada
Diversey GmbH
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Filing date
Publication date
Application filed by Diversey Corp Canada, Diversey GmbH filed Critical Diversey Corp Canada
Priority to AT86303884T priority Critical patent/ATE49694T1/en
Publication of EP0208403A1 publication Critical patent/EP0208403A1/en
Application granted granted Critical
Publication of EP0208403B1 publication Critical patent/EP0208403B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/48Nitro-carboxylic acids; Derivatives thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34Nitriles
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N59/00Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/26Phosphorus; Compounds thereof

Definitions

  • This invention relates to a water-dilutable disinfectant composition.
  • bromoacetic acid which is used in combination with sulfuric acid and phosphoric acid.
  • aliphatic alcohols have been described in the literature as having antimicrobial activity.
  • the invention provides disinfectant compositions which include said first and said second component.
  • composition in order to be water dilutable will also in practice contain a solubilizing agent, as more fully described below.
  • the substituted acid is preferably hydroxyacetic (glycolic) acid.
  • the alcohol which makes up the second component may be an aliphatic alcohol with six to twelve carbon atoms, preferably an alcohol containing from 8 to 12 carbon atoms.
  • Preferred alcohols are n-decanol and n-octanol, which may be used in admixture.
  • composition and substituted acetic acid is glycolic acid and the alcohol is n-decanol and/or n-octanol.
  • compositions according to the invention should be dilutable with water and therefore solubilising agents are preferably included to solubilise the aliphatic alcohols and to achieve stable formulations.
  • solubilising agents are not intended to contribute significantly to the microbicidal activity.
  • any compound which is capable of solubilising the alcohols can be used.
  • classes of compounds which may be used include the following:
  • These compounds may be used in salt form, e.g. as sodium salts where appropriate.
  • compositions according to the invention are active at neutral to acidic conditions. In general no pH-adjustment of the in-use solution is necessary for improving or maintaining of the antimicrobial activity.
  • pH-adjustment may be necessary.
  • the addition of inorganic or organic acids means that the pH of the use-solution becomes more independent of both the properties of the water, used for dilution, and of the C0 2 -partial pressure, which may be quite high in brewery tanks and other facilities where this disinfectant composition may be used. It may also facilitate control of the addition of the composition by measurement of conductivity.
  • the preferred acid for this purpose is phosphoric acid, but also sulfuric and nitric acid can be used.
  • Organic acids such as acetic or citric acid can be used also.
  • composition according to the invention may also contain auxiliary substances such as dyes, perfumes, surfactants and defoamers.
  • the substituted acid and the aliphatic alcohol exists an optimized ratio of both components.
  • the content of solubilising agent depends on its structure and the alcohol content.
  • composition according to the invention preferably consists of the following on a w/w basis.
  • compositions according to the invention also have a very significant activity against bacteria.
  • the formulations given in the Examples will be diluted to provide in-use solutions when required.
  • a suitable dilution will be selected to give an effective concentration.
  • the formulations may be diluted on the basis that a quantity of 0.50% by weight is diluted with water to 100% by weight, that is to say a dilution of 200. This is the dilution used for the formulations in the tests reported in the tables.
  • any suitable dilution may be used and solutions of intermediate dilutions may be prepared.
  • compositions according to the invention are useful for cold disinfecting and in particular for so-called CIP (cleaning in place) systems where the plant to be disinfected is not dismantled. This is often the case in milk-processing factories and breweries.
  • the temperature of operation is, for such cleaning, of the order of 4°C.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • Apparatus For Disinfection Or Sterilisation (AREA)

Abstract

A water-dilutable antimicrobial composition char- acterised by the following ingredients:
  • a) an alpha-substituted aliphatic acid with 2-6 carbon atoms, where the substituents are selected from chloro, iodo, cyano, nitro, amino, imino, thiohydroxy and hydroxy
  • b) an aliphatic alcohol containing six to twelve carbon atoms.
The composition may include a solubilising agent for the aliphatic alcohol.
The composition may be in the form of a concentrate, or an in-use-solution of use in the disinfection of hard surfaces in the food and beverage, including brewery, industries and also in hospitals, kitchens and in the home.

Description

  • This invention relates to a water-dilutable disinfectant composition.
  • Various compounds are known to have a disinfectant activity by themselves or in combination with other compounds. It is a continuing problem to find compositions which meet the particular requirements which are demanded in practice by industry. This invention is directed to the problem of disinfection of hard surfaces in the food and beverage, including brewery, industries and also in hospitals, kitchens and in the home.
  • Amongst the compounds known as having some antimicrobial (disinfectant) activity may be mentioned bromoacetic acid which is used in combination with sulfuric acid and phosphoric acid. Also aliphatic alcohols have been described in the literature as having antimicrobial activity.
  • We have found that the activity of a composition which contains as a first component an alpha-substituted aliphatic acid, which is a chloro, iodo, cyano, nitro, amino, imino, thiohydroxy or hydroxy carboxylic acid, and as a second component an aliphatic alcohol with six to twelve carbon atoms, is unexpectedly greater than the activity of either component alone.
  • Broadly therefore the invention provides disinfectant compositions which include said first and said second component.
  • The composition in order to be water dilutable will also in practice contain a solubilizing agent, as more fully described below.
  • Of the two components mentioned above the substituted acid is preferably hydroxyacetic (glycolic) acid. The alcohol which makes up the second component, may be an aliphatic alcohol with six to twelve carbon atoms, preferably an alcohol containing from 8 to 12 carbon atoms.
  • Preferred alcohols are n-decanol and n-octanol, which may be used in admixture.
  • In a preferred feature of the invention the composition and substituted acetic acid is glycolic acid and the alcohol is n-decanol and/or n-octanol.
  • The compositions according to the invention should be dilutable with water and therefore solubilising agents are preferably included to solubilise the aliphatic alcohols and to achieve stable formulations. The solubilising agents are not intended to contribute significantly to the microbicidal activity.
  • In principle any compound which is capable of solubilising the alcohols, can be used. Examples of classes of compounds which may be used include the following:
    • n-alkyl sulfonates
    • alkyl aryl sulfonates
    • aryl sulfonates
    • fatty alcohol ethoxylates
    • fatty alcohol ethoxypropoxylates
    • fatty alcohol sulfates
    • ethylenediamine ethoxylates
    • ethylenediamine ethoxypropoxylates
    • phenyl poly ethoxylates.
  • These compounds may be used in salt form, e.g. as sodium salts where appropriate.
  • The compositions according to the invention are active at neutral to acidic conditions. In general no pH-adjustment of the in-use solution is necessary for improving or maintaining of the antimicrobial activity.
  • However, for particular applications pH-adjustment may be necessary. The addition of inorganic or organic acids means that the pH of the use-solution becomes more independent of both the properties of the water, used for dilution, and of the C02-partial pressure, which may be quite high in brewery tanks and other facilities where this disinfectant composition may be used. It may also facilitate control of the addition of the composition by measurement of conductivity.
  • Therefore a certain acid content of the formulation will widen the range of applications.
  • The preferred acid for this purpose is phosphoric acid, but also sulfuric and nitric acid can be used. Organic acids such as acetic or citric acid can be used also.
  • The composition according to the invention may also contain auxiliary substances such as dyes, perfumes, surfactants and defoamers.
  • For each composition according to the invention the substituted acid and the aliphatic alcohol exists an optimized ratio of both components. The content of solubilising agent depends on its structure and the alcohol content.
  • The composition according to the invention preferably consists of the following on a w/w basis.
    • a) Chloro, iodo, cyano, nitro, amino, imino, thiohydroxy and/or hydroxy carboxylic acid; 0.4 - 70% (preferably 0.4 - 50.0%)
    • b) Aliphatic alcohol C 6-C 12; 0.1 - 50% (preferably 1.0 - 40.0%)
    • c) Solubilising agent for the alcohol; 0 - 50% (preferably 5.0 - 15%)
    • d) Inorganic or organic acids for pH-adjustment of the use-solution: 0 - 90% (preferably 5 to 60%)
    • e) Auxiliary substances such as dyes, perfumes, surfactants and defoamers, water.
  • The following examples of concentrates containing 2-hydroxy acetic acid (glycolic acid), in which the percentages are on a weight basis, are given by way of illustration only:
    • Concentrates
      Figure imgb0001
  • The antimicrobial activity of the active components of the composition by themselves and in combination were tested and the results are given in the following table. In this table there is also shown a mixture of 2-hydroxyacetic acid, n-decanol and n-decylsulfonate sodium salt which is according to the invention.
    Figure imgb0002
    Figure imgb0003
  • The comparative experiments were carried out on yeast species (Saccharomyces cerevisiae) since these are more difficult to kill than bacteria. The compositions according to the invention also have a very significant activity against bacteria.
  • The results demonstrate the unexpectedly higher activity obtained by the combination of the two active ingredients.
  • The formulations given in the Examples will be diluted to provide in-use solutions when required. A suitable dilution will be selected to give an effective concentration. Thus, for example the formulations may be diluted on the basis that a quantity of 0.50% by weight is diluted with water to 100% by weight, that is to say a dilution of 200. This is the dilution used for the formulations in the tests reported in the tables.
  • However, any suitable dilution may be used and solutions of intermediate dilutions may be prepared.
  • The compositions according to the invention are useful for cold disinfecting and in particular for so- called CIP (cleaning in place) systems where the plant to be disinfected is not dismantled. This is often the case in milk-processing factories and breweries. The temperature of operation is, for such cleaning, of the order of 4°C.

Claims (15)

1. A water-dilutable antimicrobial composition characterised by the following ingredients:
a) an alpha-substituted aliphatic acid with 2-6 carbon atoms, where the substituents are selected from chloro, iodo, cyano, nitro, amino, imino, thiohydroxy and hydroxy
b) an aliphatic alcohol containing six to twelve carbon atoms.
2. A composition as claimed in claim 1 in which the substituted aliphatic acid is monohydroxyacetic acid.
3. A composition as claimed in claim 1 or claim 2 in which the alcohol contains from 8 to 12 carbon atoms.
4. A composition as claimed in claim 3 in which the alcohol is n-decanol and/or n-octanol.
5. A composition as claimed in any of claims 1 to 4 in which the composition also includes a solubilising agent for the aliphatic alcohol.
6. A composition as claimed in claim 5 in which the solubilising agent is one or more of the following: fatty alcohol ethoxylates, fatty alcohol ethoxypropoxylates, ethylenediamine ethoxylates, n-alkylsulfonates, alkyl aryl sulfonates, aryl sulfonates, fatty alcohol sulfonates and phenyl poly ethoxylates.
7. A composition as claimed in any of claims 1 to 6 which also contains an inorganic or organic acid.
8. A composition as claimed in claim 7 in which the acid is phosphoric acid.
9. A composition as claimed in any of claims 1 to 8 in which the ratio of the substituted aliphatic acid to the alcohol is optimized.
10. A composition as claimed in any of claims 1 to 9 in the form of a concentrate.
11. An in-use solution or a solution of intermediate concentration made by the dilution of a composition as claimed in claim 10 with water.
12. A composition as claimed in any of claims 1 to 11 consisting of the following, on a w/w basis:
Figure imgb0004
13. A composition as claimed in claim 1 substantially. as herein described with reference to any one of the examples.
14. A method of disinfecting surfaces which comprises applying to said surface as an in-use solution a composition as claimed in any of claims 1 to 13.
15. Surfaces disinfected by the method of claim 14.
EP86303884A 1985-06-05 1986-05-22 Water-dilutable disinfectant composition Expired - Lifetime EP0208403B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT86303884T ATE49694T1 (en) 1985-06-05 1986-05-22 WATER-DILUBLE SANITIZING COMPOSITION.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB858514243A GB8514243D0 (en) 1985-06-05 1985-06-05 Water-dilutable disinfectant composition
GB8514243 1985-06-05

Publications (2)

Publication Number Publication Date
EP0208403A1 true EP0208403A1 (en) 1987-01-14
EP0208403B1 EP0208403B1 (en) 1990-01-24

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Country Status (4)

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AT (1) ATE49694T1 (en)
DE (1) DE3668406D1 (en)
GB (1) GB8514243D0 (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994000550A1 (en) * 1992-06-24 1994-01-06 Henkel Kommanditgesellschaft Auf Aktien Use of isethionic acid in cleaning and disinfecting agents
WO1998000012A1 (en) * 1996-07-02 1998-01-08 Boaz Shitzer Agricultural compositions containing glycolic acid
BE1011314A3 (en) * 1997-08-05 1999-07-06 Sopura Sa DISINFECTANT COMPOSITION.
WO1999051093A1 (en) * 1998-04-06 1999-10-14 Innoscent Ltd. Oral antimicrobial and anti-odor compositions
US6124241A (en) * 1998-10-29 2000-09-26 Auxien Corporation Method for increasing plant productivity using glutamic acid and glycolic acid
US6331505B1 (en) 1998-10-29 2001-12-18 Emerald Bioagriculture Corporation Method for increasing plant productivity using glutamic acid and glycolic acid
US6432883B1 (en) 2000-04-20 2002-08-13 Emerald Bioagriculture Corporation Methods of treating plants with glycolic acid
WO2007142967A2 (en) * 2006-05-31 2007-12-13 The Dial Corporation Alcohol-containing antimicrobial compositions having improved efficacy
WO2011017367A3 (en) * 2009-08-06 2011-06-16 Anitox Corporation Water and feed preservative
US10021901B2 (en) 2011-11-30 2018-07-17 Anitox Corporation Antimicrobial mixture of aldehydes, organic acids and fatty acid esters

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007142919A2 (en) 2006-05-30 2007-12-13 The Dial Corporation Compositions having a high antiviral effeicacy
MX2008015336A (en) 2006-06-02 2008-12-16 Dial Corp Method of inhibiting the transmission of influenza virus.

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4040977A (en) * 1973-10-16 1977-08-09 Sterling Drug Inc. Preservative and disinfectant
GB2087724A (en) * 1980-09-26 1982-06-03 Ueno Seiyaku Oyo Kenkyujo Kk Bactericide or foods and food processing machines or utensils

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4040977A (en) * 1973-10-16 1977-08-09 Sterling Drug Inc. Preservative and disinfectant
GB2087724A (en) * 1980-09-26 1982-06-03 Ueno Seiyaku Oyo Kenkyujo Kk Bactericide or foods and food processing machines or utensils

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
BRAUWELT, vol. 122, no. 37, September 1982, pages 1608-1615, Nürnberg, DE; M.D. ERNST et al.: "Bierschädliche Bakterien, tolerieren oder gezielt eliminieren?" *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994000550A1 (en) * 1992-06-24 1994-01-06 Henkel Kommanditgesellschaft Auf Aktien Use of isethionic acid in cleaning and disinfecting agents
WO1998000012A1 (en) * 1996-07-02 1998-01-08 Boaz Shitzer Agricultural compositions containing glycolic acid
BE1011314A3 (en) * 1997-08-05 1999-07-06 Sopura Sa DISINFECTANT COMPOSITION.
WO1999051093A1 (en) * 1998-04-06 1999-10-14 Innoscent Ltd. Oral antimicrobial and anti-odor compositions
US6124241A (en) * 1998-10-29 2000-09-26 Auxien Corporation Method for increasing plant productivity using glutamic acid and glycolic acid
US6331505B1 (en) 1998-10-29 2001-12-18 Emerald Bioagriculture Corporation Method for increasing plant productivity using glutamic acid and glycolic acid
US6432883B1 (en) 2000-04-20 2002-08-13 Emerald Bioagriculture Corporation Methods of treating plants with glycolic acid
WO2007142967A2 (en) * 2006-05-31 2007-12-13 The Dial Corporation Alcohol-containing antimicrobial compositions having improved efficacy
WO2007142967A3 (en) * 2006-05-31 2008-09-04 Dial Corp Alcohol-containing antimicrobial compositions having improved efficacy
WO2011017367A3 (en) * 2009-08-06 2011-06-16 Anitox Corporation Water and feed preservative
US10785975B2 (en) 2009-08-06 2020-09-29 Anitox Corporation Water and feed antimicrobial preservative
US10021901B2 (en) 2011-11-30 2018-07-17 Anitox Corporation Antimicrobial mixture of aldehydes, organic acids and fatty acid esters

Also Published As

Publication number Publication date
EP0208403B1 (en) 1990-01-24
DE3668406D1 (en) 1990-03-01
ATE49694T1 (en) 1990-02-15
GB8514243D0 (en) 1985-07-10

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